ES2249595T3 - Derivados de imidazoles que modulan los canales sodicos. - Google Patents
Derivados de imidazoles que modulan los canales sodicos.Info
- Publication number
- ES2249595T3 ES2249595T3 ES02745529T ES02745529T ES2249595T3 ES 2249595 T3 ES2249595 T3 ES 2249595T3 ES 02745529 T ES02745529 T ES 02745529T ES 02745529 T ES02745529 T ES 02745529T ES 2249595 T3 ES2249595 T3 ES 2249595T3
- Authority
- ES
- Spain
- Prior art keywords
- imidazole
- radical
- biphenyl
- linear
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 69
- 125000001424 substituent group Chemical group 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000005843 halogen group Chemical group 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 19
- 208000002193 Pain Diseases 0.000 claims abstract description 18
- 239000004305 biphenyl Substances 0.000 claims abstract description 18
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 230000036407 pain Effects 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 206010015037 epilepsy Diseases 0.000 claims abstract description 7
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 5
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 4
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- 230000033764 rhythmic process Effects 0.000 claims abstract description 4
- 208000006011 Stroke Diseases 0.000 claims abstract description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
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- -1 post-herpetic pain Chemical compound 0.000 description 92
- 238000002844 melting Methods 0.000 description 19
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- 239000000843 powder Substances 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 108010052164 Sodium Channels Proteins 0.000 description 10
- 102000018674 Sodium Channels Human genes 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 239000006071 cream Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 238000009739 binding Methods 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- AKWDQJGINZPVTA-UHFFFAOYSA-N 2-[[4-(2-methylpropyl)phenyl]methyl]-5-(4-phenylphenyl)-1h-imidazole Chemical compound C1=CC(CC(C)C)=CC=C1CC1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CN1 AKWDQJGINZPVTA-UHFFFAOYSA-N 0.000 description 2
- DJDWXDSQUIVYCH-UHFFFAOYSA-N 2-hexyl-5-[4-(2-methylpropyl)phenyl]-1h-imidazole Chemical compound N1C(CCCCCC)=NC(C=2C=CC(CC(C)C)=CC=2)=C1 DJDWXDSQUIVYCH-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- CMUYENAAZXDZQM-UHFFFAOYSA-N acetic acid;nonane Chemical compound CC(O)=O.CCCCCCCCC CMUYENAAZXDZQM-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 210000003710 cerebral cortex Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KEAGRYYGYWZVPC-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanone Chemical compound CC(C)CC1=CC=C(C(C)=O)C=C1 KEAGRYYGYWZVPC-UHFFFAOYSA-N 0.000 description 1
- QQYJGTNVPTUIRP-UHFFFAOYSA-N 2-(1-phenylethyl)-5-(4-phenylphenyl)-1h-imidazole Chemical compound C=1C=CC=CC=1C(C)C(NC=1)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 QQYJGTNVPTUIRP-UHFFFAOYSA-N 0.000 description 1
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- DWQGVMAZXFPKFB-UHFFFAOYSA-N 2-(2-methylpropyl)-5-phenyl-1h-imidazole Chemical compound N1C(CC(C)C)=NC=C1C1=CC=CC=C1 DWQGVMAZXFPKFB-UHFFFAOYSA-N 0.000 description 1
- PPZOEJFEHZJIHU-UHFFFAOYSA-N 2-(3-cyclohexylpropyl)-5-(4-phenylphenyl)-1h-imidazole Chemical compound N=1C(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CNC=1CCCC1CCCCC1 PPZOEJFEHZJIHU-UHFFFAOYSA-N 0.000 description 1
- DBIGQNHMYZOGHI-UHFFFAOYSA-N 2-(cyclohexylmethyl)-5-(4-fluorophenyl)-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1=CNC(CC2CCCCC2)=N1 DBIGQNHMYZOGHI-UHFFFAOYSA-N 0.000 description 1
- LAHDQEJNOQBNSA-UHFFFAOYSA-N 2-(cyclohexylmethyl)-5-(4-phenylphenyl)-1h-imidazole Chemical compound N=1C(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CNC=1CC1CCCCC1 LAHDQEJNOQBNSA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
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- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Networks Using Active Elements (AREA)
- Detergent Compositions (AREA)
- Molds, Cores, And Manufacturing Methods Thereof (AREA)
- Control Of Transmission Device (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0107820A FR2825926A1 (fr) | 2001-06-14 | 2001-06-14 | Derives d'imidazoles modulant les canaux sodiques |
| FR0107820 | 2001-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2249595T3 true ES2249595T3 (es) | 2006-04-01 |
Family
ID=8864329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02745529T Expired - Lifetime ES2249595T3 (es) | 2001-06-14 | 2002-06-14 | Derivados de imidazoles que modulan los canales sodicos. |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7157483B2 (da) |
| EP (1) | EP1401432B1 (da) |
| JP (1) | JP2005500297A (da) |
| KR (1) | KR20040030672A (da) |
| CN (1) | CN1535148A (da) |
| AT (1) | ATE304354T1 (da) |
| BR (1) | BR0210285A (da) |
| CA (1) | CA2449916A1 (da) |
| CZ (1) | CZ297321B6 (da) |
| DE (1) | DE60206171T2 (da) |
| DK (1) | DK1401432T3 (da) |
| ES (1) | ES2249595T3 (da) |
| FR (1) | FR2825926A1 (da) |
| HU (1) | HUP0400195A3 (da) |
| IS (1) | IS2367B (da) |
| MX (1) | MXPA03011508A (da) |
| NO (1) | NO20035553D0 (da) |
| NZ (1) | NZ529741A (da) |
| PL (1) | PL366722A1 (da) |
| RU (1) | RU2296565C2 (da) |
| WO (1) | WO2002102375A2 (da) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004210711B2 (en) * | 2003-02-12 | 2010-07-08 | Transtech Pharma, Inc. | Substituted azole derivatives as therapeutic agents |
| ZA200507752B (en) * | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
| BRPI0416639A (pt) * | 2003-11-19 | 2007-01-16 | Metabasis Therapeutics Inc | tiromiméticos contendo fósforo |
| AU2006249350B2 (en) | 2003-11-19 | 2012-02-16 | Metabasis Therapeutics, Inc. | Thyromimetics for the treatment of fatty liver diseases |
| CN102746336B (zh) | 2005-06-29 | 2015-08-19 | 施瑞修德制药公司 | 氨基磷酸酯烷化剂前体药物 |
| AU2006322844A1 (en) * | 2005-12-07 | 2007-06-14 | Ramot At Tel Aviv University Ltd. | Chemical derivatives of jasmonate, pharmaceutical compositions and methods of use thereof |
| US8247439B2 (en) * | 2005-12-07 | 2012-08-21 | Sepal Pharma Ltd. | Jasmonate derivatives, pharmaceutical compositions and methods of use thereof |
| US9284274B2 (en) | 2005-12-07 | 2016-03-15 | Ramot At Tel-Aviv University Ltd. | Chemical derivatives of jasmonate, pharmaceutical compositions and methods of use thereof |
| EP2114157B1 (en) | 2006-12-26 | 2021-05-26 | ImmunoGenesis, Inc. | Phosphoramidate alkylator prodrug for the treatment of cancer |
| US7883898B2 (en) * | 2007-05-07 | 2011-02-08 | General Electric Company | Method and apparatus for measuring pH of low alkalinity solutions |
| US8188080B2 (en) * | 2007-10-17 | 2012-05-29 | Sanford-Burnham Medical Research Institute | VHR protein tyrosine phosphatase inhibitors, compositions and methods of use |
| US8815892B2 (en) | 2008-03-25 | 2014-08-26 | Affectis Pharmaceuticals Ag | P2X7R antagonists and their use |
| EP2105164B1 (en) * | 2008-03-25 | 2011-01-12 | Affectis Pharmaceuticals AG | Novel P2X7R antagonists and their use |
| KR101602985B1 (ko) * | 2008-10-06 | 2016-03-11 | 시코쿠가세이고교가부시키가이샤 | 2-벤질-4-(2,4-디클로로페닐)-5-메틸이미다졸 화합물 |
| US9284252B2 (en) | 2009-06-09 | 2016-03-15 | Sepal Pharma Ltd. | Use of jasmonate ester derivatives for treating benign hyperproliferative skin disorders |
| JP5368244B2 (ja) * | 2009-10-14 | 2013-12-18 | 四国化成工業株式会社 | ２−（２，４−ジクロロベンジル）−４−アリール−５−メチルイミダゾール化合物 |
| JP5368263B2 (ja) * | 2009-11-04 | 2013-12-18 | 四国化成工業株式会社 | ４−（２，４−ジクロロフェニル）−５−メチルイミダゾール化合物 |
| JP5368271B2 (ja) * | 2009-11-20 | 2013-12-18 | 四国化成工業株式会社 | ４−（４−ビフェニリル）−２−（２，４−ジクロロベンジル）イミダゾールおよび表面処理液 |
| CN110198719A (zh) | 2016-11-21 | 2019-09-03 | 维京治疗公司 | 治疗糖原贮积病的方法 |
| KR102600115B1 (ko) | 2017-06-05 | 2023-11-09 | 바이킹 테라퓨틱스 인코포레이티드 | 섬유증 치료를 위한 조성물 |
| AU2019238090B2 (en) | 2018-03-22 | 2024-08-01 | Viking Therapeutics, Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
| US12102646B2 (en) | 2018-12-05 | 2024-10-01 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
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| WO2025231324A1 (en) * | 2024-05-02 | 2025-11-06 | Genep Inc. | Imidazole compounds and their use as sodium channel inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1046248A (en) * | 1962-08-02 | 1966-10-19 | Benger Lab Ltd | Substituted imidazoles |
| AU518569B2 (en) * | 1979-08-07 | 1981-10-08 | Farmos-Yhtyma Oy | 4-benzyl- and 4-benzoyl imidazole derivatives |
| CN1093535C (zh) * | 1994-09-26 | 2002-10-30 | 盐野义制药株式会社 | 咪唑衍生物 |
| CN1284066A (zh) * | 1997-12-04 | 2001-02-14 | 阿勒根销售公司 | 对α2B或2B/2C肾上腺素能受体具有激动剂样活性的取代咪唑衍生物 |
| US6003118A (en) * | 1997-12-16 | 1999-12-14 | Acer Laboratories Inc. | Method and apparatus for synchronizing clock distribution of a data processing system |
| ATE467620T1 (de) * | 1999-03-26 | 2010-05-15 | Euro Celtique Sa | Arylsubstituierte pyrazole, imidazole, oxazole, thiazole und pyrrole, sowie deren verwendung |
| AR024077A1 (es) * | 1999-05-25 | 2002-09-04 | Smithkline Beecham Corp | Compuestos antibacterianos |
| TWI283577B (en) * | 1999-10-11 | 2007-07-11 | Sod Conseils Rech Applic | Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof |
| WO2001044201A1 (en) * | 1999-12-16 | 2001-06-21 | Schering Corporation | Substituted imidazole neuropeptide y y5 receptor antagonists |
-
2001
- 2001-06-14 FR FR0107820A patent/FR2825926A1/fr not_active Withdrawn
-
2002
- 2002-06-14 KR KR10-2003-7016257A patent/KR20040030672A/ko not_active Abandoned
- 2002-06-14 CZ CZ20033550A patent/CZ297321B6/cs not_active IP Right Cessation
- 2002-06-14 CN CNA028111842A patent/CN1535148A/zh active Pending
- 2002-06-14 RU RU2004100843/15A patent/RU2296565C2/ru not_active IP Right Cessation
- 2002-06-14 WO PCT/FR2002/002039 patent/WO2002102375A2/fr not_active Ceased
- 2002-06-14 CA CA002449916A patent/CA2449916A1/fr not_active Abandoned
- 2002-06-14 US US10/480,977 patent/US7157483B2/en not_active Expired - Fee Related
- 2002-06-14 MX MXPA03011508A patent/MXPA03011508A/es active IP Right Grant
- 2002-06-14 HU HU0400195A patent/HUP0400195A3/hu unknown
- 2002-06-14 DK DK02745529T patent/DK1401432T3/da active
- 2002-06-14 NZ NZ529741A patent/NZ529741A/en unknown
- 2002-06-14 ES ES02745529T patent/ES2249595T3/es not_active Expired - Lifetime
- 2002-06-14 AT AT02745529T patent/ATE304354T1/de not_active IP Right Cessation
- 2002-06-14 PL PL02366722A patent/PL366722A1/xx not_active Application Discontinuation
- 2002-06-14 BR BR0210285-4A patent/BR0210285A/pt not_active IP Right Cessation
- 2002-06-14 JP JP2003504962A patent/JP2005500297A/ja active Pending
- 2002-06-14 EP EP02745529A patent/EP1401432B1/fr not_active Expired - Lifetime
- 2002-06-14 DE DE60206171T patent/DE60206171T2/de not_active Expired - Fee Related
-
2003
- 2003-12-08 IS IS7067A patent/IS2367B/is unknown
- 2003-12-12 NO NO20035553A patent/NO20035553D0/no not_active Application Discontinuation
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2005
- 2005-11-17 US US11/281,864 patent/US7402602B2/en not_active Expired - Fee Related
-
2006
- 2006-11-27 US US11/604,522 patent/US20070099975A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7157483B2 (en) | 2007-01-02 |
| HUP0400195A3 (en) | 2004-10-28 |
| ATE304354T1 (de) | 2005-09-15 |
| US20040198792A1 (en) | 2004-10-07 |
| CN1535148A (zh) | 2004-10-06 |
| MXPA03011508A (es) | 2004-03-18 |
| HUP0400195A2 (hu) | 2004-07-28 |
| US20060069146A1 (en) | 2006-03-30 |
| CA2449916A1 (fr) | 2002-12-27 |
| DE60206171D1 (de) | 2005-10-20 |
| DK1401432T3 (da) | 2006-02-06 |
| NZ529741A (en) | 2006-10-27 |
| FR2825926A1 (fr) | 2002-12-20 |
| US7402602B2 (en) | 2008-07-22 |
| IS7067A (is) | 2003-12-08 |
| RU2004100843A (ru) | 2005-04-10 |
| CZ297321B6 (cs) | 2006-11-15 |
| EP1401432B1 (fr) | 2005-09-14 |
| US20070099975A1 (en) | 2007-05-03 |
| RU2296565C2 (ru) | 2007-04-10 |
| DE60206171T2 (de) | 2006-06-22 |
| NO20035553D0 (no) | 2003-12-12 |
| BR0210285A (pt) | 2004-06-29 |
| KR20040030672A (ko) | 2004-04-09 |
| JP2005500297A (ja) | 2005-01-06 |
| WO2002102375A2 (fr) | 2002-12-27 |
| IS2367B (is) | 2008-06-15 |
| WO2002102375A3 (fr) | 2003-09-25 |
| PL366722A1 (en) | 2005-02-07 |
| CZ20033550A3 (cs) | 2005-05-18 |
| EP1401432A2 (fr) | 2004-03-31 |
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